Show legend Show as text

Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140628,IEDB_140629,IEDB_141794,IEDB_141806,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_232584,IEDB_232585,IEDB_742521,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

• Article ID: 380
  Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" - APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
  

  Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.

  Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics

  NCBI PubMed ID: 9048864
  Publication DOI: 10.1111/j.1699-0463.1996.tb04951.x
  Journal NLM ID: 8803400
  Publisher: Copenhagen: Munksgaard
  Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
  
   
  
  Yersinia pseudotuberculosis
  CSDB ID 31515 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lipoteichoate derivative
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_135614,IEDB_140628,IEDB_140629,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_153543,IEDB_153755,IEDB_158538,IEDB_158555,IEDB_1597446,IEDB_161523,IEDB_232584,IEDB_232585,IEDB_241101,IEDB_241118,IEDB_420421,IEDB_423115,IEDB_742521,IEDB_857742,IEDB_983931,SB_192

• Article ID: 2581
  Fischer W, Rösel P, Koch HU "Effect of alanine ester substitution and other structural features of lipoteichoic acids on their inhibitory activity against autolysins of Staphylococcus aureus" - Journal of Bacteriology 146(2) (1981) 467-475
  

  Native substitution with the D-alanine ester of lipoteichoic acids (LTAs) affects their immunological properties, the capacity to bind divalent cations, and LTA carrier activity. In this study we tested the influence of the D-alanine ester on anti-autolytic activity, using extracellular autolysin from Staphylococcus aureus and nine LTAs with alanine/phosphorus molar ratios of between 0.23 and 0.71. The inhibitory activity, highest with alanine-free LTA, exponentially decreased with increasing alanine content, approaching zero at substitutions of greater than 0.6. Correspondingly, dipolar ionic phospholipids were not inhibitory, in contrast to negatively charged ones. Glycosylation of LTA up to an extent of 0.5 did not depress inhibitory activity, and even at a degree of 0.8 the effect was comparatively small. On comparison of LTAs from various sources, differences in lipid structures and chain lengths were without effect. The inhibitory activity drastically decreased when the glycolipid carried a single glycerophosphate residue or the hydrophilic chain had the unusual structure [6→Gal(α1→6)Gal(α1→3)Gro-(2 comes from 1 αGal)-P]n, in which digalactosyl moieties connect the α-galactosylated glycerophosphate units. Principally, the same results were obtained with the more complex system of autolysis of S. aureus cells. We hypothesize that the anti-autolytic activity of LTA resides in a sequence of glycerophosphate units and that the negative charges of appropriately spaced phosphodiester groups play a crucial role. The alanine ester effect is discussed with respect to the putative in vivo regulation of autolysins by LTA.

  NCBI PubMed ID: 6111553
  Publication DOI: 10.1128/JB.146.2.467-475.1981
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Institutions: Institut für Physiologische Chemie, Universität Erlangen-Nürnberg, D-8520 Erlangen, Federal Republic of Germany
  
   
  
  Streptococcus faecalis ATCC 9790
  CSDB ID 131724 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: R-form LPS
Contained glycoepitopes: IEDB_130650,IEDB_135614,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140628,IEDB_140629,IEDB_141794,IEDB_141806,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153543,IEDB_153755,IEDB_158555,IEDB_190606,IEDB_232584,IEDB_232585,IEDB_241101,IEDB_423115,IEDB_742521,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

• Article ID: 2681
  Ovodov YS, Gorshkova RP, Tomshich SV, Komandrova NA, Zubkov VA, Kalmykova EN, Isakov VV "Chemical and Immunochemical studies on lipopolysaccharides of some Yersinia species - A review of some recent investigations" - Journal of Carbohydrate Chemistry 11 (1992) 21-35
  

  The present paper revealed the results of some recent chemical and immunochemical studies of the lipopolysaccharides from various species and erologie variants of Yersinia genus as follows: Y. pseudotuberculosis IIC and VII; Y. enterocolitica 0:1, 2a, 3; 0:2a, 2b, 3; 0:3; 0:4, 32; 0:5; 0:5,27; 0:6,31; 0:7,8; 0:19,8; 0:8; Y. frederiksenii 0:16,29; Y. intermedia 0:4,33; Y. aldovae.

  Publication DOI: 10.1080/07328309208016139
  Journal NLM ID: 8218151
  Publisher: Marcel Dekker
  Institutions: The Pacific Institute of Bioorganic Chemistry, Far East Branch of the USSR Academy of Sciences, 690022, Vladivostok, U.S.S.R
  Methods: 13C NMR, 1H NMR
  
   
  
  Yersinia pseudotuberculosis
  CSDB ID 137844 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: cell-surface polysaccharide, pentaglycosyl phosphate repeating unit cell-surface polysaccharide, rhamnoglucan PSI, PS1, cell-surface polysaccharide PS-I, PSI, PSI repeating unit
Compound class: cell wall polysaccharide, lipoteichoic acid
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_189515,IEDB_189517,IEDB_225177,IEDB_232583,IEDB_232584,IEDB_232585,IEDB_885823,IEDB_983931,SB_192

• Article ID: 3470
  Ganeshapillai J, Vinogradov E, Rousseau J, Weese JS, Monteiro MA "Clostridium difficile cell-surface polysaccharides composed of pentaglycosyl and hexaglycosyl phosphate repeating units" - Carbohydrate Research 343(4) (2008) 703-710
  

  Clostridium difficile is a Gram-positive bacterium that is known to be a cause of enteric diseases in humans. It is the leading cause of antibiotic-associated diarrhea and pseudomembranous colitis. Recently, large outbreaks of C. difficile-associated diarrhea have been reported internationally, and there have been reports of increases in severe disease, mortality and relapse rates. At the moment, there is no vaccine against C. difficile, and the medical prevention of C. difficile infection is mostly based on the prophylactic use of antibiotics; however, this has led to an increase in the incidence of the disease. Here, we describe the chemical structure of C. difficile cell-surface polysaccharides. The polysaccharides of three C. difficile strains were structurally analyzed; ribotype 027 (North American pulsotype 1) strain was observed to express two polysaccharides, one was composed of a branched pentaglycosyl phosphate repeating unit: [→4)-α-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[α-L-Rhap-(1→3]-α-D-Glcp-(1→2)-α-D-Glcp-(1→P] and the other was composed of a hexaglycosyl phosphate repeating unit: [→6)-β-D-Glcp-(1→3)-β-D-GalpNAc-(1→4)-α-D-Glcp-(1→4)-[β-D-Glcp-(1→]-β-D-GalpNAc-(1→3)-α-D-Manp-(1→P]. The latter polysaccharide was also observed to be produced by strains MOH900 and MOH718. The results described here represent the first literature report describing the covalent chemical structures of C. difficile cell-surface polysaccharides, of which PS-II appears to be a regular C. difficile antigen. These C. difficile teichoic-acid-like polysaccharides will be tested as immunogens in vaccine preparations in a rat and horse model.

  Structural characterization, Clostridium difficile, Teichoic-acid polysaccharide

  NCBI PubMed ID: 18237724
  Publication DOI: 10.1016/j.carres.2008.01.002
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: monteiro@uoguelph.ca
  Institutions: Department of Chemistry, University of Guelph, Guelph, ON, Canada N1G 2W1
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, 31P NMR, composition analysis
  
   
  
  Clostridium difficile O27
  CSDB ID 22647 (all data & tools)
• Article ID: 4275
  Bertolo L, Boncheff AG, Ma Z, Chen YH, Wakeford T, Friendship RM, Rosseau J, Weese JS, Chu M, Mallozzi M, Vedantam G, Monteiro MA "Clostridium difficile carbohydrates: glucan in spores, PSII common antigen in cells, immunogenicity of PSII in swine and synthesis of a dual C. difficile-ETEC conjugate vaccine" - Carbohydrate Research 354 (2012) 79-86
  

  Clostridium difficile is responsible for severe diarrhea in humans that may cause death. Spores are the infectious form of C. difficile, which germinate into toxin-producing vegetative cells in response to bile acids. Recently, we discovered that C. difficile cells possess three complex polysaccharides (PSs), named PSI, PSII, and PSIII, in which PSI was only associated with a hypervirulent ribotype 027 strain, PSII was hypothesized to be a common antigen, and PSIII was a water-insoluble polymer. Here, we show that (i) C. difficile spores contain, at least in part, a D-glucan, (ii) PSI is not a ribotype 027-unique antigen, (iii) common antigen PSII may in part be present as a low molecular weight lipoteichoic acid, (iv) selective hydrolysis of PSII yields single PSII repeat units, (v) the glycosyl diester-phosphate linkage affords high flexibility to PSII, and (vi) that PSII is immunogenic in sows. Also, with the intent of creating a dual anti-diarrheal vaccine against C. difficile and enterotoxin Escherichia coli (ETEC) infections in humans, we describe the conjugation of PSII to the ETEC-associated LTB enterotoxin.

  conjugate vaccine, glucan, Clostridium difficile, spores, PSI, PSII

  NCBI PubMed ID: 22533919
  Publication DOI: 10.1016/j.carres.2012.03.032
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: monteiro@uoguelph.ca (M.A. Monteiro)
  Institutions: Department of Chemistry, University of Guelph, Guelph, ON, Canada
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, SDS-PAGE, sugar analysis, 31P NMR, MD simulations, immunochemical methods, conjugation
  
   
  
  Clostridium difficile 027
  CSDB ID 28310 (all data & tools)
• Article ID: 4378
  Reid CW, Vinogradov E, Li J, Jarrell HC, Logan SM, Brisson JR "Structural characterization of surface glycans from Clostridium difficile" - Carbohydrate Research 354 (2012) 65-73
  

  Whole-cell high-resolution magic angle spinning (HR-MAS) NMR was employed to survey the surface polysaccharides of a group of clinical and environmental isolates of Clostridium difficile. Results indicated that a highly conserved surface polysaccharide profile among all strains studied. Multiple additional peaks in the anomeric region were also observed which prompted further investigation. Structural characterization of the isolated surface polysaccharides from two strains confirmed the presence of the conserved water soluble polysaccharide originally described by Ganeshapillai et al. which was composed of a hexaglycosyl phosphate repeat consisting of [→6)-β-D-Glcp-(1-3)-β-D-GalpNAc-(1-4)-α-D-Glcp-(1-4)-[β-D-Glcp(1-3]-β-D-GalpNAc-(1-3)-α-D-Manp-(1-P→]. In addition, analysis of phenol soluble polysaccharides revealed a similarly conserved lipoteichoic acid (LTA) which could be detected on whole cells by HR-MAS NMR. Conventional NMR and mass spectrometry analysis indicated that the structure of this LTA consisted of the repeat unit [→6)-α-D-GlcpNAc-(1-3)-[→P-6]-α-D-GlcpNAc-(1-2)-D-GroA] where GroA is glyceric acid. The repeating units were linked by a phosphodiester bridge between C-6 of the two GlcNAc residues (6-P-6). A minor component consisted of GlcpN-(1-3) instead of GlcpNAc-(1-3) in the repeat unit. Through a 6-6 phosphodiester bridge this polymer was linked to →6)-β-D-Glcp-(1-6)-β-D-Glcp-(1-6)-β-D-Glcp-(1-1)-Gro, with glycerol (Gro) substituted by fatty acids. This is the first report of the utility of HR-MAS NMR in the examination of surface carbohydrates of Gram positive bacteria and identification of a novel LTA structure from Clostridium difficile.

  capsular polysaccharide, lipoteichoic acid, Clostridium difficile, lipocarbohydrate, High-resolution magic angle spinning (HRMAS) NMR

  NCBI PubMed ID: 22560631
  Publication DOI: 10.1016/j.carres.2012.02.002
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: S.M. Logan
  Institutions: National Research Council-Institute for Biological Sciences, 100 Sussex Drive, Ottawa, ON, Canada K1A 0R6
  Methods: 13C NMR, 1H NMR, de-O-acylation, sugar analysis, 31P NMR, HF treatment, CE-MS/MS, HR-MAS NMR
  
   
  
  Clostridium difficile O27
  CSDB ID 28604 (all data & tools)
• Article ID: 4542
  Jiao Y, Ma Z, Hodgins D, Pequegnat B, Bertolo L, Arroyo L, Monteiro MA "Clostridium difficile PSI polysaccharide: synthesis of pentasaccharide repeating block, conjugation to exotoxin B subunit, and detection of natural anti-PSI IgG antibodies in horse serum" - Carbohydrate Research 378 (2013) 15-25
  

  Clostridium difficile is the most common cause of antimicrobial-associated diarrhea in humans and may cause death. Previously, we discovered that C. difficile expresses three polysaccharides, named PSI, PSII, and PSIII. It has now been established that PSII is a conserved antigen abundantly present on the cell-surface and biofilm of C. difficile. In contrast, the expression of PSI and PSIII appears to be stochastic processes. In this work, the total chemical synthesis of the PSI pentasaccharide repeating unit carrying a linker at the reducing end, α-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→2)-α-D-Glcp-(1→O(CH2)5NH2, was achieved by a linear synthesis strategy from four monosaccharide building blocks. The synthesized PSI pentasaccharide was conjugated to a subunit of C. difficile exotoxin B yielding a potential dual C. difficile vaccine. More significantly, sera from healthy horses were shown to contain natural anti-PSI IgG antibodies that detected both the synthetic non-phosphorylated PSI repeat and the native PSI polysaccharide, with a slightly higher recognition of the native PSI polysaccharide.

  vaccine, Clostridium difficile, Anti-PSI IgG antibodies, C. difficile PSI polysaccharide, C. difficile Toxin B conjugate

  NCBI PubMed ID: 23597587
  Publication DOI: 10.1016/j.carres.2013.03.018
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: M.A. Monteiro
  Institutions: Department of Chemistry, University of Guelph, Guelph, ON, Canada
  Methods: 13C NMR, 1H NMR, SDS-PAGE, TLC, ELISA, chemical synthesis, conjugation
  
   
  
  Clostridium difficile O27
  CSDB ID 29214 (all data & tools)
• Article ID: 4572
  Martin CE, Weishaupt MW, Seeberger PH "Progress toward developing a carbohydrate-conjugate vaccine against Clostridium difficile ribotype 027: synthesis of the cell-surface polysaccharide PS-I repeating unit" - Chemical Communications 47(37) (2011) 10260-10262
  

  Clostridium difficile strain ribotype 027 is a hypervirulent pathogen that is responsible for recent, severe outbreaks of serious nosocomial infections. As a foundation for the development of a preventative carbohydrate-based vaccine, we have synthesized a pentasaccharide cell wall repeating unit from PS-I unique to this strain, by the linear assembly of four monosaccharide building blocks.

  synthesis, repeating unit, pentasaccharide, vaccine, nosocomial infections, Clostridium difficile

  Publication DOI: 10.1039/C1CC13614C
  Journal NLM ID: 9610838
  Publisher: Cambridge: Royal Society of Chemistry
  Correspondence: peter.seeberger@mpikg.mpg.de
  Institutions: Max Planck Institute of Colloids and Interfaces, Department of Biomolecular Systems, Am Muhlenberg 1, 14476 Potsdam, Germany
  Methods: 13C NMR, 1H NMR, chemical synthesis, chemical methods, glycosylation
  
   
  
  Clostridium difficile O27
  CSDB ID 29273 (all data & tools)
• Article ID: 5188
  Micoli F, Costantino P, Adamo R "Potential targets for next generation anti-microbial glycoconjugate vaccines" - FEMS Microbiology Reviews 42(3) (2018) 388-423
  

  Cell surface carbohydrates have been proven optimal targets for vaccine development. Conjugation of polysaccharides to a carrier protein triggers a T-cell dependent immune response to the glycan moiety. Licensed glycoconjugate vaccines are produced by chemical conjugation of capsular polysaccharides to prevent meningitis caused by meningococcus, pneumococcus and Haemophilus influenzae type b. However, other classes of carbohydrates (O-antigens, exopolysaccharides, wall/teichoic acids) represent attractive targets for developing vaccines.Recent analysis from WHO/CHO underpins alarming concern towards antibiotic resistant bacteria, such as the so called ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa and Enterobacter spp.) and additional pathogens such as Clostridium difficile and Group A Streptococcus. Fungal infections are also becoming increasingly invasive for immunocompromised patients or hospitalized individuals. Other emergencies could derive from bacteria which spread during environmental calamities (Vibrio cholerae) or with potential as bioterrorism weapons (Burkholderia pseudomallei and mallei, Francisella tularensis). Vaccination could aid reducing the use of broad spectrum antibiotics and provide protection by herd immunity also to individuals who are not vaccinated.This review analyses structural and functional differences of the polysaccharides exposed on the surface of emerging pathogenic bacteria, combined with medical need and technological feasibility of corresponding glycoconjugate vaccines.

  carbohydrates, glycoconjugates, vaccines, glycoengineering, antimicrobial resistance

  NCBI PubMed ID: 29547971
  Publication DOI: 10.1093/femsre/fuy011
  Journal NLM ID: 8902526
  Publisher: Oxford University Press
  Correspondence: Roberto Adamo
  Institutions: GSK Vaccines Institute for Global Health (GVGH), Via Fiorentina 1, 53100 Siena
  
   
  
  Clostridium difficile
  CSDB ID 12687 (all data & tools)
• Article ID: 5740
  Campanero-Rhodes MA, Palma AS, Menendez M, Solis D "Microarray Strategies for Exploring Bacterial Surface Glycans and Their Interactions With Glycan-Binding Proteins" - Frontiers in Microbiology 10 (2020) 2909
  

  Bacterial surfaces are decorated with distinct carbohydrate structures that may substantially differ among species and strains. These structures can be recognized by a variety of glycan-binding proteins, playing an important role in the bacteria cross-talk with the host and invading bacteriophages, and also in the formation of bacterial microcolonies and biofilms. In recent years, different microarray approaches for exploring bacterial surface glycans and their recognition by proteins have been developed. A main advantage of the microarray format is the inherent miniaturization of the method, which allows sensitive and high-throughput analyses with very small amounts of sample. Antibody and lectin microarrays have been used for examining bacterial glycosignatures, enabling bacteria identification and differentiation among strains. In addition, microarrays incorporating bacterial carbohydrate structures have served to evaluate their recognition by diverse host/phage/bacterial glycan-binding proteins, such as lectins, effectors of the immune system, or bacterial and phagic cell wall lysins, and to identify antigenic determinants for vaccine development. The list of samples printed in the arrays includes polysaccharides, lipopoly/lipooligosaccharides, (lipo)teichoic acids, and peptidoglycans, as well as sequence-defined oligosaccharide fragments. Moreover, microarrays of cell wall fragments and entire bacterial cells have been developed, which also allow to study bacterial glycosylation patterns. In this review, examples of the different microarray platforms and applications are presented with a view to give the current state-of-the-art and future prospects in this field.

  antibodies, immune system, lectins, vaccine development, microarrays, bacterial glycans, bacterial interactions

  NCBI PubMed ID: 32010066
  Publication DOI: 10.3389/fmicb.2019.02909
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: Dolores Solis
  Institutions: Instituto de Quimica Fisica Rocasolano, Consejo Superior de Investigaciones Cientificas, Madrid, Spain, Centro de Investigacion Biomedica en Red de Enfermedades Respiratorias, Instituto de Salud Carlos III, Madrid, Spain, UCIBIO, Department of Chemistry, Faculty of Science and Technology, NOVA University of Lisbon, Lisbon, Portuga
  
   
  
  Clostridium difficile
  CSDB ID 32072 (all data & tools)
• Article ID: 6211
  Del Bino L, Osterlid KE, Wu DY, Nonne F, Romano MR, Codée J, Adamo R "Synthetic Glycans to Improve Current Glycoconjugate Vaccines and Fight Antimicrobial Resistance" - Chemical Reviews 122(20) (2022) 15672-15716
  

  Antimicrobial resistance (AMR) is emerging as the next potential pandemic. Different microorganisms, including the bacteria Acinetobacter baumannii, Clostridioides difficile, Escherichia coli, Enterococcus faecium, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, non-typhoidal Salmonella, and Staphylococcus aureus, and the fungus Candida auris, have been identified by the WHO and CDC as urgent or serious AMR threats. Others, such as group A and B Streptococci, are classified as concerning threats. Glycoconjugate vaccines have been demonstrated to be an efficacious and cost-effective measure to combat infections against Haemophilus influenzae, Neisseria meningitis, Streptococcus pneumoniae, and, more recently, Salmonella typhi. Recent times have seen enormous progress in methodologies for the assembly of complex glycans and glycoconjugates, with developments in synthetic, chemoenzymatic, and glycoengineering methodologies. This review analyzes the advancement of glycoconjugate vaccines based on synthetic carbohydrates to improve existing vaccines and identify novel candidates to combat AMR. Through this literature survey we built an overview of structure-immunogenicity relationships from available data and identify gaps and areas for further research to better exploit the peculiar role of carbohydrates as vaccine targets and create the next generation of synthetic carbohydrate-based vaccines.

  carbohydrates, glycan, glycoconjugate vaccine

  NCBI PubMed ID: 35608633
  Publication DOI: 10.1021/acs.chemrev.2c00021
  Journal NLM ID: 2985134R
  Publisher: Chem Rev
  Correspondence: J. Codée ; R. Adamo
  Institutions: GSK, R&D, 53100 Siena, Italy, Leiden Institute of Chemistry, Leiden University, 2300 RA Leiden, The Netherlands
  
   
  
  Clostridioides difficile
  CSDB ID 20886 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: 5-amino-pentanyl
Trivial name: PS1, cell-surface polysaccharide PS-I
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_189515,IEDB_189517,IEDB_225177,IEDB_232583,IEDB_232584,IEDB_232585,IEDB_885823,IEDB_983931,SB_192

• Article ID: 4542
  Jiao Y, Ma Z, Hodgins D, Pequegnat B, Bertolo L, Arroyo L, Monteiro MA "Clostridium difficile PSI polysaccharide: synthesis of pentasaccharide repeating block, conjugation to exotoxin B subunit, and detection of natural anti-PSI IgG antibodies in horse serum" - Carbohydrate Research 378 (2013) 15-25
  

  Clostridium difficile is the most common cause of antimicrobial-associated diarrhea in humans and may cause death. Previously, we discovered that C. difficile expresses three polysaccharides, named PSI, PSII, and PSIII. It has now been established that PSII is a conserved antigen abundantly present on the cell-surface and biofilm of C. difficile. In contrast, the expression of PSI and PSIII appears to be stochastic processes. In this work, the total chemical synthesis of the PSI pentasaccharide repeating unit carrying a linker at the reducing end, α-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→2)-α-D-Glcp-(1→O(CH2)5NH2, was achieved by a linear synthesis strategy from four monosaccharide building blocks. The synthesized PSI pentasaccharide was conjugated to a subunit of C. difficile exotoxin B yielding a potential dual C. difficile vaccine. More significantly, sera from healthy horses were shown to contain natural anti-PSI IgG antibodies that detected both the synthetic non-phosphorylated PSI repeat and the native PSI polysaccharide, with a slightly higher recognition of the native PSI polysaccharide.

  vaccine, Clostridium difficile, Anti-PSI IgG antibodies, C. difficile PSI polysaccharide, C. difficile Toxin B conjugate

  NCBI PubMed ID: 23597587
  Publication DOI: 10.1016/j.carres.2013.03.018
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: M.A. Monteiro
  Institutions: Department of Chemistry, University of Guelph, Guelph, ON, Canada
  Methods: 13C NMR, 1H NMR, SDS-PAGE, TLC, ELISA, chemical synthesis, conjugation
  
   
  
  Clostridium difficile O27
  CSDB ID 29589 (all data & tools)
• Article ID: 4572
  Martin CE, Weishaupt MW, Seeberger PH "Progress toward developing a carbohydrate-conjugate vaccine against Clostridium difficile ribotype 027: synthesis of the cell-surface polysaccharide PS-I repeating unit" - Chemical Communications 47(37) (2011) 10260-10262
  

  Clostridium difficile strain ribotype 027 is a hypervirulent pathogen that is responsible for recent, severe outbreaks of serious nosocomial infections. As a foundation for the development of a preventative carbohydrate-based vaccine, we have synthesized a pentasaccharide cell wall repeating unit from PS-I unique to this strain, by the linear assembly of four monosaccharide building blocks.

  synthesis, repeating unit, pentasaccharide, vaccine, nosocomial infections, Clostridium difficile

  Publication DOI: 10.1039/C1CC13614C
  Journal NLM ID: 9610838
  Publisher: Cambridge: Royal Society of Chemistry
  Correspondence: peter.seeberger@mpikg.mpg.de
  Institutions: Max Planck Institute of Colloids and Interfaces, Department of Biomolecular Systems, Am Muhlenberg 1, 14476 Potsdam, Germany
  Methods: 13C NMR, 1H NMR, chemical synthesis, chemical methods, glycosylation
  
   
  
  Clostridium difficile O27
  CSDB ID 29646 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure ; 1743 [M+Na]+
Aglycon: Asn136-X-Set/Thr of GAP50 glycoprotein
Compound class: N-glycan
Contained glycoepitopes: IEDB_115576,IEDB_130701,IEDB_135614,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_140628,IEDB_140629,IEDB_141111,IEDB_141793,IEDB_141806,IEDB_141807,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141836,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_153212,IEDB_153219,IEDB_153220,IEDB_153543,IEDB_153755,IEDB_158538,IEDB_158555,IEDB_164174,IEDB_232584,IEDB_232585,IEDB_241101,IEDB_420421,IEDB_423115,IEDB_742521,IEDB_857742,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72,SB_74,SB_77,SB_85

• Article ID: 5921
  Fauquenoy S, Hovasse A, Sloves PJ, Morelle W, Dilezitoko Alayi T, Slomianny K, Werkmeister E, Schaeffer C, Van Dorsselaer A, Tomavo S "Unusual N-glycan structures required for trafficking Toxoplasma gondii GAP50 to the inner membrane complex regulate host cell entry through parasite motility" - Molecular and Cellular Proteomics 10(9) (2011) M111.008953
  

  Toxoplasma gondii motility, which is essential for host cell entry, migration through host tissues, and invasion, is a unique form of actin-dependent gliding. It is powered by a motor complex mainly composed of myosin heavy chain A, myosin light chain 1, gliding associated proteins GAP45, and GAP50, the only integral membrane anchor so far described. In the present study, we have combined glycomic and proteomic approaches to demonstrate that all three potential N-glycosylated sites of GAP50 are occupied by unusual N-glycan structures that are rarely found on mature mammalian glycoproteins. Using site-directed mutagenesis, we show that N-glycosylation is a prerequisite for GAP50 transport from the endoplasmic reticulum to the Golgi apparatus and for its subsequent delivery into the inner complex membrane. Assembly of key partners into the gliding complex, and parasite motility are severely impaired in the unglycosylated GAP50 mutants. Furthermore, comparative affinity purification using N-glycosylated and unglycosylated GAP50 as bait identified three novel hypothetical proteins including the recently described gliding associated protein GAP40, and we demonstrate that N-glycans are required for efficient binding to gliding partners. Collectively, these results provide the first detailed analyses of T. gondii N-glycosylation functions that are vital for parasite motility and host cell entry.

  infection, glycoproteins, N-glycosylation, N-glycans, Parasite, Toxoplasma, Toxoplasma gondii, N-glycan

  NCBI PubMed ID: 21610105
  Publication DOI: 10.1074/mcp.M111.008953
  Journal NLM ID: 101125647
  Publisher: Bethesda, MD: ASBMB
  Correspondence: Stan.Tomavo@pasteur-lille.fr
  Institutions: Center for Infection and Immunity of Lille, CNRS UMR 8204, INSERM U 1019, Institut Pasteur de Lille, Université Lille Nord de France, 59000 Lille, France
  Methods: SDS-PAGE, Western blotting, MALDI-TOF MS, genetic methods, enzymatic digestion, affinity chromatography, cloning, immunofluorescence microscopy, LC-MS/MS, confocal microscopy, gene knockin, nanoLC-MS, cell invasion assay, cell proliferation assay
  
   
  
  Toxoplasma gondii GAP50
  CSDB ID 4893 (all data & tools)

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Structure type: oligomer
Aglycon: 5-amino-pentyl, spacer-CRM197
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_189515,IEDB_189517,IEDB_225177,IEDB_232583,IEDB_232584,IEDB_232585,IEDB_885823,IEDB_983931,SB_192

• Article ID: 6211
  Del Bino L, Osterlid KE, Wu DY, Nonne F, Romano MR, Codée J, Adamo R "Synthetic Glycans to Improve Current Glycoconjugate Vaccines and Fight Antimicrobial Resistance" - Chemical Reviews 122(20) (2022) 15672-15716
  

  Antimicrobial resistance (AMR) is emerging as the next potential pandemic. Different microorganisms, including the bacteria Acinetobacter baumannii, Clostridioides difficile, Escherichia coli, Enterococcus faecium, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, non-typhoidal Salmonella, and Staphylococcus aureus, and the fungus Candida auris, have been identified by the WHO and CDC as urgent or serious AMR threats. Others, such as group A and B Streptococci, are classified as concerning threats. Glycoconjugate vaccines have been demonstrated to be an efficacious and cost-effective measure to combat infections against Haemophilus influenzae, Neisseria meningitis, Streptococcus pneumoniae, and, more recently, Salmonella typhi. Recent times have seen enormous progress in methodologies for the assembly of complex glycans and glycoconjugates, with developments in synthetic, chemoenzymatic, and glycoengineering methodologies. This review analyzes the advancement of glycoconjugate vaccines based on synthetic carbohydrates to improve existing vaccines and identify novel candidates to combat AMR. Through this literature survey we built an overview of structure-immunogenicity relationships from available data and identify gaps and areas for further research to better exploit the peculiar role of carbohydrates as vaccine targets and create the next generation of synthetic carbohydrate-based vaccines.

  carbohydrates, glycan, glycoconjugate vaccine

  NCBI PubMed ID: 35608633
  Publication DOI: 10.1021/acs.chemrev.2c00021
  Journal NLM ID: 2985134R
  Publisher: Chem Rev
  Correspondence: J. Codée ; R. Adamo
  Institutions: GSK, R&D, 53100 Siena, Italy, Leiden Institute of Chemistry, Leiden University, 2300 RA Leiden, The Netherlands
  
   
  
  Clostridioides difficile
  CSDB ID 20889 (all data & tools)

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Structure type: structural motif or average structure
Contained glycoepitopes: IEDB_115576,IEDB_128161,IEDB_130701,IEDB_133966,IEDB_134620,IEDB_134621,IEDB_135614,IEDB_136095,IEDB_136104,IEDB_137340,IEDB_137472,IEDB_137485,IEDB_1394182,IEDB_1397514,IEDB_140116,IEDB_140628,IEDB_140629,IEDB_141111,IEDB_141793,IEDB_141795,IEDB_141806,IEDB_141807,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_142357,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_147452,IEDB_147453,IEDB_147454,IEDB_149137,IEDB_149176,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_153543,IEDB_153755,IEDB_153756,IEDB_1539315,IEDB_158538,IEDB_158555,IEDB_161166,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_164479,IEDB_164480,IEDB_174840,IEDB_190606,IEDB_232584,IEDB_232585,IEDB_241101,IEDB_420417,IEDB_420418,IEDB_420419,IEDB_420420,IEDB_420421,IEDB_423115,IEDB_558866,IEDB_558867,IEDB_558868,IEDB_558869,IEDB_742521,IEDB_76933,IEDB_857742,IEDB_857743,IEDB_885812,IEDB_983930,IEDB_983931,SB_136,SB_191,SB_192,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72,SB_77

• Article ID: 6749
  Fontaine T, Simenel C, Dubreucq G, Adam O, Delepierre M, Lemoine J, Vorgias CE, Diaquin M, Latge JP "Molecular organization of the alkali-insoluble fraction of Aspergillus fumigatus cell wall" - Journal of Biological Chemistry 275 (2000) 27594-27607
  

  Physical and biological properties of the fungal cell wall are determined by the composition and arrangement of the structural polysaccharides. Cell wall polymers of fungi are classically divided into two groups depending on their solubility in hot alkali. We have analyzed the alkali-insoluble fraction of the Aspergillus fumigatus cell wall, which is the fraction believed to be responsible for fungal cell wall rigidity. Using enzymatic digestions with recombinant endo-β-1,3-glucanase and chitinase, fractionation by gel filtration, affinity chromatography with immobilized lectins, and high performance liquid chromatography, several fractions that contained specific interpolysaccharide covalent linkages were isolated. Unique features of the A. fumigatuscell wall are (i) the absence of β-1,6-glucan and (ii) the presence of a linear β-1,3/1,4-glucan, never previously described in fungi. Galactomannan, chitin, and β-1,3-glucan were also found in the alkali-insoluble fraction. The β-1,3-glucan is a branched polymer with 4% of β-1,6 branch points. Chitin, galactomannan, and the linear β-1,3/1,4-glucan were covalently linked to the nonreducing end of β-1,3-glucan side chains. As in Saccharomyces cerevisiae, chitin was linked via a β-1,4 linkage to β-1,3-glucan. The data obtained suggested that the branching of β-1,3-glucan is an early event in the construction of the cell wall, resulting in an increase of potential acceptor sites for chitin, galactomannan, and the linear β-1,3/1,4-glucan.

  Publication DOI: 10.1074/jbc.M909975199
  Journal NLM ID: 2985121R
  WWW link: http://www.jbc.org/content/275/36/27594.abstract
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: tfontain@pasteur.fr
  Institutions: Laboratoire des Aspergillus, Institut Pasteur, 25 rue du Docteur Roux, 75724 Paris cedex 15, France, Laboratoire de Résonance Magnétique Nucléaire, Institut Pasteur, 28 rue du Docteur Roux, 75724 Paris cedex 15, France, Laboratoire de Chimie Biologique, Universitédes Sciences et Technologie de Lille Flandres-Artois 59655 Villeneuve d'Ascq cedex, France, University of Athens, Department of Biology, Division of Biochemistry and Molecular Biology GR-15701, Athens, Greece
  Methods: gel filtration, 13C NMR, 1H NMR, GLC-MS, acid hydrolysis, GLC, mild acid hydrolysis, HPAEC, enzymatic digestion, 15N NMR, acetolysis, TOCSY, methylation analysis, DQF-COSY, MALDI-TOF-MS, phenol-sulfuric acid procedure, Johnson procedure, lectin affinity chromatography, gHSQC-TOCSY
  
   
  
  Aspergillus fumigatus CBS 144-89
  CSDB ID 40488 (all data & tools)
• Article ID: 6762
  Bernard M, Latge JP "Aspergillus fumigatus cell wall: composition and biosynthesis" - Medical Mycology 39 (2001) 9-17
  

  Analysis of the cell wall of Aspergillus fumigatus is guided by obvious biological reasons: the cell wall protects the fungus against the aggressive human defense reactions, it harbours most of the fungal antigens and it represents a potential drug target. This review will discuss our current understanding of the structural organization of the polysaccharides constitutive of the cell wall of A. fumigatus [α and β(1,3)-glucans, chitin, galactomannan, and β(1,3),(1,4)-glucan] and of the enzymes (synthases, transglycosidases, and glycosyl hydrolases) responsible for their biosynthesis and remodelling. Comparative analysis of the cell wall of the conidium and mycelium also provides insights on their respective roles during the pathogenic life of this fungal species.

  transferase, cell wall, synthase, hydrolase, Aspergillus fumigatus, conidium, mycelium

  Publication DOI: 10.1080/mmy.39.1.9.17
  Journal NLM ID: 9815835
  Publisher: Oxford: Oxford University Press
  Correspondence: jplatge@pasteur.fr
  Institutions: Unité des Aspergillus, Institut Pasteur, Paris, France
  
   
  
  Aspergillus fumigatus
  CSDB ID 40511 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Compound class: cell wall polysaccharide, galactoglucomannan
Contained glycoepitopes: IEDB_115576,IEDB_128161,IEDB_130701,IEDB_133966,IEDB_134620,IEDB_134621,IEDB_135614,IEDB_136095,IEDB_136104,IEDB_137340,IEDB_137472,IEDB_137485,IEDB_1397514,IEDB_140116,IEDB_140628,IEDB_140629,IEDB_141111,IEDB_141793,IEDB_141795,IEDB_141806,IEDB_141807,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_142357,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_147452,IEDB_147453,IEDB_147454,IEDB_149137,IEDB_149176,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_153543,IEDB_153755,IEDB_153756,IEDB_1539315,IEDB_158538,IEDB_158555,IEDB_161166,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_164479,IEDB_164480,IEDB_174840,IEDB_190606,IEDB_232584,IEDB_232585,IEDB_241101,IEDB_420417,IEDB_420418,IEDB_420419,IEDB_420420,IEDB_420421,IEDB_423115,IEDB_558866,IEDB_558867,IEDB_558868,IEDB_558869,IEDB_742521,IEDB_76933,IEDB_857742,IEDB_857743,IEDB_885812,IEDB_983930,IEDB_983931,SB_136,SB_191,SB_192,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72,SB_77

• Article ID: 7500
  Gow NAR, Latge JP, Munro CA "The fungal cell wall: structure, biosynthesis, and function" - Microbiology Spectrum 5(3) (2017) FUNK-0035
  

  The molecular composition of the cell wall is critical for the biology and ecology of each fungal species. Fungal walls are composed of matrix components that are embedded and linked to scaffolds of fibrous load-bearing polysaccharides. Most of the major cell wall components of fungal pathogens are not represented in humans, other mammals, or plants, and therefore the immune systems of animals and plants have evolved to recognize many of the conserved elements of fungal walls. For similar reasons the enzymes that assemble fungal cell wall components are excellent targets for antifungal chemotherapies and fungicides. However, for fungal pathogens, the cell wall is often disguised since key signature molecules for immune recognition are sometimes masked by immunologically inert molecules. Cell wall damage leads to the activation of sophisticated fail-safe mechanisms that shore up and repair walls to avoid catastrophic breaching of the integrity of the surface. The frontiers of research on fungal cell walls are moving from a descriptive phase defining the underlying genes and component parts of fungal walls to more dynamic analyses of how the various components are assembled, cross-linked, and modified in response to environmental signals. This review therefore discusses recent advances in research investigating the composition, synthesis, and regulation of cell walls and how the cell wall is targeted by immune recognition systems and the design of antifungal diagnostics and therapeutics.

  NCBI PubMed ID: 28513415
  Publication DOI: 10.1128/microbiolspec.FUNK-0035-2016
  Journal NLM ID: 101634614
  Publisher: Washington, DC: ASM Press
  Correspondence: n.gow@abdn.ac.uk
  Institutions: Unité des Aspergillus, Institut Pasteur, Paris, France, Aberdeen Fungal Group, Institute of Medical Sciences, University of Aberdeen, Aberdeen, UK
  
   
  
  Aspergillus fumigatus
  CSDB ID 43192 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure ; 2330000
Trivial name: polysaccharide LDP-CP
Contained glycoepitopes: IEDB_115576,IEDB_130701,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_140116,IEDB_141794,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_232584,IEDB_232585,IEDB_76933,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_197,SB_31,SB_44,SB_67,SB_7,SB_72

• Article ID: 9359
  Li K, Wang L, Hu Y, Zhu Z "Structural characterization and protective effect on PC12 cells against H2O2-induced oxidative damage of a polysaccharide extracted from mycelia of Lactarius deliciosus Gray" - International Journal of Biological Macromolecules (2022) 1815-1825
  

  The crude polysaccharide LDP was extracted from mycelia of Lactarius deliciosus Gray and then purified by DEAE-52 cellulose and Sephadex G-200 to obtain a novel polysaccharide named LDP-CP. LDP-CP was mainly composed of mannose, glucose and galactose with an average molecular weight of 2.33 × 103 kDa. The structure of LDP-CP was determined by FT-IR, methylation and NMR analysis, and the results showed that the sugar linkage units of LDP-CP were composed of (1 → 3)-linked β-D-Manp, (1→2,4)-linked α-D-Manp, (1→)-linked α-D-Manp, (1→4)-linked β-D-Glcp, (1→2)-linked β-D-Manp, (1→4,6)-linked α-D-Manp, (1→4)-linked α-D-Galp, (1→2,3)-linked α-D-Glcp and (1→)-linked α-D-Glcf. The protective effects of LDP and LDP-CP on PC12 cells against H2O2-induced oxidative injury were exhibited by enhancing cell viability and morphological protection. The improvement to the level of LDH, SOD and GSH further indicated that LDP and LDP-CP had ability to alleviate H2O2-induced oxidative damage on PC12 cells. The polysaccharides in Lactarius deliciosus Gray mycelia exhibited the great advantages in the management of oxidative toxicity, which indicated that the polysaccharides can be further developed in application of natural functional food source.

  polysaccharide, Lactarius deliciosus Gray, oxidative damage

  NCBI PubMed ID: 35487375
  Publication DOI: 10.1016/j.ijbiomac.2022.04.154
  Journal NLM ID: 7909578
  Publisher: Butterworth-Heinemann
  Correspondence: Z. Zhu
  Institutions: Key Laboratory of Food Nutrition and Safety, Ministry of Education-Tianjin Key Laboratory of Food Nutrition and Safety, Tianjin University of Science and Technology, Tianjin, China, State Key Laboratory of Food Nutrition and Safety, Tianjin University of Science and Technology, Tianjin, China, College of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin, China, College of Public Health, Zunyi Medical University, Guizhou, China
  Methods: 13C NMR, 1H NMR, methylation, GC-MS, sugar analysis, FTIR, HPLC, extraction, optical rotation measurement, statistical analysis, cell viability assay, SEM, ion exchange chromatography, tissue isolation, oxidative stress, DrawGlycan-SNFG
  
   
  
  Lactarius deliciosus (L.) Gray
  CSDB ID 51636 (all data & tools)